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Patent 2621631 Summary

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(12) Patent Application: (11) CA 2621631
(54) English Title: SOLID FORMULATION OF FUNGICIDAL MIXTURES
(54) French Title: FORMULATION DE MELANGES FONGICIDES SOLIDES
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 37/50 (2006.01)
  • A01N 25/14 (2006.01)
  • A01N 43/653 (2006.01)
  • A01N 47/04 (2006.01)
  • B01J 2/20 (2006.01)
(72) Inventors :
  • WOLF, HILMAR (Germany)
(73) Owners :
  • BAYER CROPSCIENCE AKTIENGESELLSCHAFT (Germany)
(71) Applicants :
  • BAYER CROPSCIENCE AKTIENGESELLSCHAFT (Germany)
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 2006-08-31
(87) Open to Public Inspection: 2007-03-15
Examination requested: 2011-08-29
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP2006/008512
(87) International Publication Number: WO2007/028537
(85) National Entry: 2008-03-06

(30) Application Priority Data:
Application No. Country/Territory Date
102005042879.7 Germany 2005-09-09

Abstracts

English Abstract




The invention relates to highly concentrated WG-formulations of fungicidal
mixtures, containing trifloxystrobine and an active substance which is
selected from tebuconazole and tolylfluanide, in addition to a dispersing
agent from the series Baykanol ~ SL, Reax ~ 907 and Reax ~ 88B. The invention
also relates to a method for the production thereof and to the use thereof for
combating fungi.


French Abstract

L'invention concerne des formulations WG hautement concentrées de mélanges fongicides contenant de la trifloxystrobine et un agent actif sélectionné parmi tébuconazole et tolylfluanide, ainsi qu'un agent de dispersion de la série Baykanol ® SL, Reax ® 907 et Reax ® 88B. La présente invention porte également sur un procédé de production et sur l'utilisation de ces formulations pour lutter contre les champignons.

Claims

Note: Claims are shown in the official language in which they were submitted.





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Claims


1. Composition containing
- trifloxystrobin

- at least one further active substance selected from tebuconazole and
tolylfluanid,

- at least one dispersant selected from the group consisting of Baykanol ®
SL, Reax
® 907 and Reax ® 88 B.


2. Composition according to Claim 1, characterized in that it furthermore
contains at least
one wetter and inert filler.


3. Composition according to one or more of Claims 1 to 2, characterized in
that it contains
further formulation auxiliaries from the groups of the emulsifiers,
surfactants, the antifoam
agents, the preservatives, the antioxidants, the colorants and/or the inert
fillers.


4. Composition according to one or more of Claims 1 to 3, characterized in
that Baykanol
® SL is employed as the dispersant.


5. Composition according to one or more of Claims 1 to 4, characterized in
that it contains
at least one further fungicidal active substance.


6. Process for the preparation of a WG formulation according to one or more of
Claims 1 to
5, characterized in that the formulation is prepared by low-pressure extrusion
at
temperatures below 60°C.


7. Use of a WG formulation according to one or more of Claims 1 to 5 for the
application of
the agrochemical active substances present on plants and/or their environment.


8. Composition, characterized in that it contains a WG formulation according
to one or more
of Claims 1 to 5 and extenders and/or surface-active agents.


9. Use of a formulation according to one or more of Claims 1 to 5 for
controlling fungi.

Description

Note: Descriptions are shown in the official language in which they were submitted.



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Solids formulation of fungicidal mixtures

The invention relates to solids formulations (in particular water-dispersible
granules) of mixtures
of trifloxystrobin (TFS) with tebuconazole or tolylfluanid (Euparen M), to a
process for their
preparation, and to their use for applying the active substances which they
contain.

EP-A-0831698 discloses mixtures of TFS with tebuconazole, but only teaches WG
formulations
with an active substance content of 15% by weight. The preparation of mixtures
with higher
concentrations is only disclosed in the form of powders or as a suspension
concentrate.

The preparation of highly concentrated WG formulations with the formulation
auxiliaries
mentioned in the prior art gives formulations which have undesirable
properties. Thus, the low
melting point of the active substance mixture results in the formation of
large amounts of wet-
screening residues which, when the spray mixture is later applied, lead to
plugging of the nozzles.
Surprisingly, it has now been found that the present, highly concentrated
formulations have
particularly advantageous properties. Thus, their preparation only generates
very small amounts of
wet-screening residues, they can be extruded readily and they have
particularly high suspension
stability.

The present invention accordingly provides compositions containing:
= trifloxystrobin (component 1)

= at least one further active substance selected from tebuconazole and
tolylfluanid (component II)
= at least one dispersant selected from the group consisting of Baykanol OO
SL, Reax 907 and
Reax 88B

In the compositions according to the invention, components I and II are
present in weight ratios of
from 1: 30 to 12 : 1, preferably I : 20 to 5 : 1, especially preferably 1: 15
to 1: 1. If the
composition according to the invention contains tebuconazole and tolylfluanid,
these substances
together are considered as component II.

Components I and II together are hereinbelow referred to as active substance.
A preferred embodiment of the invention are compositions containing

= 50 - 75%, preferably 60 - 75%, especially preferably 65 - 75% active
substance

= 5 - 20%, preferably 10 - 20%, especially preferably 10 - 15% at least one
dispersant selected
from the group consisting of Baykanol 9 SL, Reax 9 907 and Reax 9 88B


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Unless otherwise specified, percentages are understood as being per cent by
weight.

An embodiment of the invention which must be emphasized are those compositions
in which
Baykanol SL is employed as the dispersant.

A further embodiment of the invention which must be emphasized are those
compositions in which
Baykanol SL is employed as the dispersant and tebuconazole as component lI.

A further embodiment of the invention which must be emphasized are those
compositions in which
Baykanol SL is employed as the dispersant and tolylfluanid as component II.

It has also been found that the compositions according to the invention can be
prepared by
moistening a pulverulent mixture consisting of the active substances and the
formulation
auxiliaries, subsequently granulating it by means of low-pressure extrusion
and then drying the
moist granules. The relevant apparatuses for moistening, extrusion and drying
are known to the
skilled worker. During the preparation, care must be taken in particular that
the temperatures to
which the product is exposed are kept at lower than 60 C, and preferably lower
than 50 C, in all
process steps.

This process is also subject matter of the invention.

Finally, it has been found that the compositions according to the invention
are highly suitable for
the application of the agrochemical active substances present on plants and/or
their environment.
This method is also subject matter of the invention.

If appropriate, the compositions according to the invention contain further
formulation auxiliaries,
for example if appropriate substances from the groups of the emulsifiers, the
anionic or nonionic
surfactants, the antifoam agents, the preservatives, the antioxidants, the
colorants and/or the inert
fillers.

Nonionic surfactants or dispersing auxiliaries which are suitable are all
substances of this type
which can usually be employed in agrochemical compositions. Those which may be
mentioned by
preference are polyethylene oxide/polypropylene oxide block copolymers,
polyethylene glycol
ethers of linear alcohols, reaction products of fatty acids with ethylene
oxide and/or propylene
oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, copolymers of
polyvinyl alcohol and
polyvinylpyrrolidone and copolymers of (meth)acrylic acid and (meth)acrylic
esters, furthermore
alkyl ethoxylates and alkylaryl ethoxylates, which can optionally be
phosphated and optionally be
neutralized with bases, examples which may be mentioned by way of example
being sorbitol
ethoxylates, and polyoxyalkyleneamine derivatives.


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Anionic surfactants which are suitable are all substances of this type which
can usually be
employed in agrochemical compositions. Preferred are alkali metal and alkaline
earth metal salts
of alkylsulphonic acids or alkylarylsulphonic acids.

A further preferred group of anionic surfactants or dispersing auxiliaries are
salts of
polystyrenesulphonic acids, salts of polyvinylsulphonic acids, salts of
naphthalenesulphonic
acid/formaldehyde condensates, salts of condensates of naphthalenesulphonic
acid,
phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.

Antifoam agents which are suitable are all substances which can usually be
employed for this
purpose in agrochemical compositions. Silicone oils and magnesium stearate are
preferred.

Preservatives which are suitable are all substances of this type which can
usually be employed for
this purpose in agrochemical compositions. Examples which may be mentioned are
Preventol
(Bayer AG) and Proxel .

Antioxidants which are suitable are all substances which can usually be
employed for this purpose
in agrochemical compositions. Butylhydroxytoluene is preferred.

Colorants which are suitable are all substances which can usually be employed
for this purpose in
agrochemical compositions. Examples which may be mentioned are titanium
dioxide, colour black,
zinc oxide and blue pigments, and also permanent red FGR.

Inert fillers which are suitable are all substances which can usually be
employed for this purpose in
agrochemical compositions. Preferred are inorganic particles such as
carbonates, silicates and
oxides, and also organic substances such as urea/formaldehyde condensates.
Examples which may
be mentioned are kaolin, rutile, silicon dioxide, what is known as highly-
disperse silica, silica gels,
and natural and synthetic silicates, and furthermore talc.

The application rate of the formulations according to the invention can be
varied within a
substantial range. It depends on the respective active substances and on their
content in the
compositions.

Using the compositions according to the invention, the fungicidal active
substance mixtures can be
applied particularly advantageously to plants and/or their environment.

All plants and plant parts can be treated with the compositions according to
the invention. In this
context, plants are understood as meaning all plants and plant populations,
such as desired and
undesired wild plants or crop plants (including naturally occurring crop
plants). Crop plants can be
plants which can be obtained by traditional breeding and optimization methods
or by


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biotechnological and recombinant methods or combinations of these methods,
including the
transgenic plants and including the plant varieties capable or not of being
protected by Plant
Breeders' Rights. Plant parts are understood as meaning all aerial and
subterranean parts and
organs of the plants, such as shoot, leaf, flower and root, examples which may
be mentioned being
leaves, needles, stalks, stems, flowers, fruiting bodies, fruits and seeds,
and roots, tubers and
rhizomes. The plant parts also include harvested material and vegetative and
generative
propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

What may be emphasized in this context is the particularly advantageous effect
of the
compositions according to the invention with regard to their use in cereal
plants such as, for
example, wheat, oats, barley, spelt, triticale and rye, but also in maize,
sorghum and millet, rice,
sugar cane, soya beans, sunflowers, potatoes, cotton, oilseed rape, canola,
tobacco, sugar beet,
fodder beet, asparagus, hops and fruit plants (comprising pome fruit such as,
for example, apples
and pears, stone fruit such as, for example, peaches, nectarines, cherries,
plums and apricots, citrus
fruits such as, for example, oranges, grapefruits, limes, lemons, kumquats,
tangerines and
satsumas, nuts such as, for example, pistachios, almonds, walnuts and pecan
nuts, tropical fruits
such as, for example, mango, paw-paw, pineapple, dates and bananas, and
grapes) and vegetables
(comprising leaf vegetables such as, for example, endives, corn salad,
Florence fennel, various
types of head lettuce and cut-and-come-again lettuce, Swiss chard, spinach and
chicory, cabbages
such as, for example, cauliflower, broccoli, Chinese leaves, borecole (curly
kale), kohlrabi,
Brussels sprouts, red cabbage, white cabbage and savoy cabbage, fruit
vegetables such as, for
example, aubergines, cucumbers, capsicums, table pumpkins, tomatoes,
courgettes and sweetcorn,
root vegetables such as, for example, celeriac, early turnips, carrots,
including yellow cultivars,
radish, small radish, beetroot, scorzonera and celery, legumes such as, for
example, peas and
beans, and bulb vegetables such as, for example, leeks and onions).

The treatment according to the invention of the plants and plant parts with
the compositions
according to the invention is carried out either directly or by treating their
environment, habitat or
storage space by the customary treatment methods, for example by dipping,
spraying, vaporizing,
misting, broadcasting, painting on and, in the case of propagation material,
in particular seeds,
furthermore by coating with one or more layers.

The compositions according to the invention have very good fungicidal
properties and can be
employed for controlling phytopathogenic fungi such as Plasmodiophoromycetes,
Oomycetes,
Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and
the like.
Examples which may be mentioned, but not by limitation, are some pathogens of
fungal diseases
which come under the above generic terms:


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Diseases caused by pathogens causing powdery mildew such as, for example,
Blumeria species such as, for example, Blumeria graminis;

Podosphaera species such as, for example, Podosphaera leucotricha;
Sphaerotheca species such as, for example, Sphaerotheca fuliginea;
Uncinula species such as, for example, Uncinula necator;

diseases caused by pathogens of rust diseases such as, for example,
Gymnosporangium species such as, for example, Gymnosporangium sabinae
Hemileia species such as, for example, Hemileia vastatrix;

Phakopsora species such as, for example, Phakopsora pachyrhizi and Phakopsora
meibomiae;
Puccinia species such as, for example, Puccinia recondita or Puccinia
triticina;

Uromyces species such as, for example, Uromyces appendiculatus;

diseases caused by pathogens from the group of the Oomycetes such as, for
example,
Bremia species such as, for example, Bremia lactucae;

Peronospora species such as, for example, Peronospora pisi or P. brassicae;
Phytophthora species such as, for example, Phytophthora infestans;
Plasmopara species such as, for example, Plasmopara viticola;
Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;

Pythium species such as, for example, Pythium ultimum;
leaf spot diseases and leaf wilt caused by, for example,
Altemaria species such as, for example, Alternaria solani;
Cercospora species such as, for example, Cercospora beticola;
Cladiosporum species such as, for example, Cladiosporium cucumerinum;


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Cochliobolus species such as, for example, Cochliobolus sativus
(conidial form: Drechslera, syn: Helminthosporium);

Colletotrichum species such as, for example, Colletotrichum lindemuthanium;
Cycloconium species such as, for example, Cycloconium oleaginum;

Diaporthe species such as, for example, Diaporthe citri;
Elsinoe species such as, for example, Elsinoe fawcettii;
Gloeosporium species such as, for example, Gloeosporium laeticolor;
Glomerella species such as, for example, Glomerella cingulata;
Guignardia species such as, for example, Guignardia bidwelli;

Leptosphaeria species such as, for example, Leptosphaeria maculans;
Magnaporthe species such as, for example, Magnaporthe grisea;
Mycosphaerella species such as, for example, Mycosphaerella graminicola;
Phaeosphaeria species such as, for example, Phaeosphaeria nodorum;
Pyrenophora species such as, for example, Pyrenophora teres;

Ramularia species such as, for example, Ramularia collo-cygni;
Rhynchosporium species such as, for example, Rhynchosporium secalis;
Septoria species such as, for example, Septoria apii;

Typhula species such as, for example, Typhula incarnata;
Venturia species such as, for example, Venturia inaequalis;
root and stalk diseases, caused by, for example,

Corticium species such as, for example, Corticium graminearum;
Fusarium species such as, for example, Fusarium oxysporum;
Gaeumannomyces species such as, for example, Gaeumannomyces graminis;


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Rhizoctonia species such as, for example, Rhizoctonia solani;
Tapesia species such as, for example, Tapesia acuformis;
Thielaviopsis species such as, for example, Thielaviopsis basicola;

ear and panicle diseases (including maize cobs), caused by, for example,
Alternaria species such as, for example, Alternaria spp.;

Aspergillus species such as, for example, Aspergillus flavus;
Cladosporium species such as, for example, Cladosporium spp.;
Claviceps species such as, for example, Claviceps purpurea;
Fusarium species such as, for example, Fusarium culmorum;

Gibberella species such as, for example, Gibberella zeae;
Monographella species such as, for example, Monographella nivalis;
diseases caused by smuts such as, for example,

Sphacelotheca species such as, for example, Sphacelotheca reiliana;
Tilletia species such as, for example, Tilletia caries;

Urocystis species such as, for example, Urocystis occulta;
Ustilago species such as, for example, Ustilago nuda;
fruit rot caused by, for example,

Aspergillus species such as, for example, Aspergillus flavus;
Botrytis species such as, for example, Botrytis cinerea;

Penicillium species such as, for example, Penicillium expansum;
Sclerotinia species such as, for example, Sclerotinia sclerotiorum;
Verticilium species such as, for example, Verticilium alboatrum;

seed- and soil-borne rots and wilts, and seedling diseases, caused by, for
example,


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Fusarium species such as, for example, Fusarium culmorum;
Phytophthora species such as, for example, Phytophthora cactorum;
Pythium species such as, for example, Pythium ultimum;
Rhizoctonia species such as, for example, Rhizoctonia solani;

Sclerotium species such as, for example, Sclerotium rolfsii;
cankers, galls and witches' broom diseases, caused by, for example,
Nectria species such as, for example, Nectria galligena;

wilts caused by, for example,

Monilinia species such as, for example, Monilinia laxa;

deformations of leaves, flowers and fruits, caused by, for example,
Taphrina species such as, for example, Taphrina deformans;
degenerative diseases of woody species, caused by, for example,
Esca species such as, for example, Phaemoniella clamydospora;
flower and seed diseases, caused by, for example,

Botrytis species such as, for example, Botrytis cinerea;
diseases of plant tubers caused by, for example,

Rhizoctonia species such as, for example, Rhizoctonia solani;
diseases caused by bacteria] pathogens such as, for example,

Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae;
Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrymans;
Erwinia species such as, for example, Erwinia amylovora;

by preference, the following diseases of soya beans can be controlled:
fungal diseases on leaves, stems, pods and seeds caused by, for example,


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alternaria leaf spot (Altemaria spec. atrans tenuissima), anthracnose
(Colletotrichum
gloeosporoides dematium var. truncatum), brown spot (Septoria glycines),
cercospora leaf spot and
blight (Cercospora kikuchii), choanephora leaf blight (Choanephora
infundibulifera trispora
(Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew
(Peronospora
manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot
(Cercospora sojina),
leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot
(Phyllosticta sojaecola),
powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta
glycines),
rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust
(Phakopsora pachyrhizi), scab
(Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target
spot
(Corynespora cassiicola)

fungal diseases on roots and the stem base caused by, for example,

black root rot (Calonectria crotalariae), charcoal rot (Macrophomina
phaseolina), fusarium blight
or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium
orthoceras, Fusarium
semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus
terrestris), neocosmo-
spora (Neocosmopspora vasinfecta), pod and stem blight (Diaporthe
phaseolorum), stem canker
(Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora
megasperma), brown
stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium
irregulare,
Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root
rot, stem decay,
and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia
sclerotiorum), sclerotinia
southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis
basicola).

The examples which follow illustrate the subject matter of the invention
without limiting it.


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Examples

In an experimental series, samples of the following general composition:
25% by weight trifloxystrobin
50% by weight tebuconazole
15% by weight dispersant
10% by weight kaolin

were extruded using a Fuji Paudal laboratory extruder type DG-1 and then
subjected to
comparative examinations.

Preparation:
In the first step of the preparation, a pulverulent mixture of the above
composition is prepared by
mixing the starting components and subsequently subjecting the mixture to air-
jet grinding using
an 8 inch air-jet mill. Thereafter, the powder is inoistened in a Braun
kitchen blender by
portionwise addition of water and vigorous mixing until the powder is
homogeneously moist. The
amount of water whose addition allowed the best-possible extrusion in each
case had been
determined for each powder mixture in preliminary experiments. Depending on
the dispersant
used, the added water amounted to between 13 and 24% by weight, based on the
amount of
powder. The moistened powder is subsequently extruded by means of the
laboratory extruder, and
the moist granules are dried in a fluidized-bed dryer at an inlet air
temperature of 60 C and a waste
air temperature of approximately 35 C, the product temperature not exceeding
40 C. The drying
time varies between 2 and 12 minutes. The residual water content of the
samples is between 0.3
and 1.7% and is determined via the weight loss at 70 C using a Mettler
infrared dryer moisture
analyzer type LP 16.


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Test:

Wet screening: The residues were tested on a screen with a mesh size of 150
pm. The wet-
screening residues are of particular importance in the preparation of WG
formulations by extrusion
of low-melting active substances because the extrusion process can, as the
result of compaction
and temperature stress, give rise to product fractions which upon the intended
use in water do not
redisperse into the primary particles and lead to plugging of the filters in
apparatuses used in
agricultural practice. As a result, spraying may have to be interrupted and
the filters subjected to
laborious cleaning. The wet-screening test is a laboratory test for assessing
the nondispersing
fractions in the formulation. In this test, the screen residue should
preferably be less than 0.05%
and especially preferably less than 0.02%.

A 2-litre glass beaker equipped with stirrer is charged with 1000 ml of tap
water, and 50 g of the
WG formulation are introduced while stirring at 500 revolutions per minute.
The mixture is stirred
for 150 seconds and the suspension is then poured onto a screen with a mesh
size of 150 pm, the
residues in the glass beaker are rinsed off with a small amount of tap water
and the mixture is
washed with a jet of water (rubber hose with an internal diameter of approx.
10 mm; flow rate of
the tap water: approx. 4-5 1/min). During this process, the fines are rinsed
through the screen. After
the screen has been rinsed for several (not more than ten) minutes, it is left
to drip, and, using
demineralized water, the residue is transferred from the screen into a
previously weighed
evaporating pan and dried at 70 C to constant weight. After cooling, the
residue is weighed and the
percentage of the residue based on the 50 g of formulation which have been
employed is
determined.

Assessment of the extrudability: The assessment of the extrudability of a
mixture is based on the
observations made during preparation of the sample. Factors which are taken
into consideration
are, for example, flowability of the moistened powder, formation of the
extrudate, disintegration of
the extrudate, heating and the like. Promising scale-up requires an assessment
of "good" or at least
"satisfactory". "Moderate" means insufficient granulation, and "poor" means
that the mixture
cannot be extruded with a laboratory extruder.

Suspension stability: The suspension stability is a measure for the
suspendability of the insoluble
constituents of the formulation in the spray mixture. Good suspension
stability ensures a
homogeneous distribution of the product and thus the uniform dosage when the
product is applied.
The suspension stability should generally amount to >/= 75%. A 1% strength
suspension of the
formulation is prepared in a 250-mi graduated cylinder by placing the
calculated amount of
granules into water, leaving the mixture to stand for 4 minutes and, after
sealing the graduated
cylinder with a rubber stopper, inverting the former 30 times by 180 within 1
minute. The rubber


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stopper is removed, and the suspension is left to stand quietly at room
temperature for precisely
30 minutes. Then, the upper 9/10 of the suspension are pipetted off and the
bottom tenth is
transferred into a weighed evaporating pan using distilled water. The content
of the pan is dried at
70 C to constant weight, which is how the sediment is determined. The amount
of suspension
(suspension stability) is calculated using the formula:
Amount of suspension = (100 - sediment) x 1.11

Unless otherwise specified, percentages in the following tables are taken to
mean per cent by
weight.

Table 1:

Example Dispersant Added water Assessment of the Wet-screening
No. (%) extrudability residue on
150- m screen (%)
1 Baykanol SL 19 good 0.010
2 Borresperse NA 21 good 0.565
3 Tersperse 2425 18 good 0.365
4 Galoryl DT 530 14 moderate 0.239
5 Kraftsperse DD-5 19 good/satisfactory 0.072
6 Kraftsperse DD-8 18 moderate 0.069
7 Kraftsperse DW-5 13 satisfactory/moderate 0.975
8 Kraftsperse EDF-450 20 moderate 0.165
9 Morwet D 425 13 moderate 0.741
Reax 88 B 21 satisfactory 0.040
11 Reax 907 22 good 0.033
12 Ufoxane 3 A 17 good/satisfactory 0.291

The results of an experimental series in which different dispersants are used
are compiled in
Table 1. The samples differ greatly regarding the wet-screening residues and
the assessment of the
extrudability. Only Examples I, 10 and 11 meet the requirement of preferably
less than 0.05% wet-
screening residues. Only Examples I and II additionally have "good"
extrudability. Only
Example I has the especially preferred wet-screening residues of less than
0.02% while
simultaneously exhibiting "good" extrudability.


CA 02621631 2008-03-06
BCS 05-3078-Foreign Countries

-13-
Table 2:

Example No. 13 14 15 16 17 18 19 20
Formtila i , - -- _ ~ ~ -- I
Trifloxystrobin [%] 6 6.3 6.3 6.3 6.3 6.3 6.3 6.3
Tolylfluanid [%] 65 62.5 62.5 62.5 62.5 62.5 62.5 62.5
Kraftsperse EDF-350 [%] 15 15 15 15
Kraftsperse EDF-450 [%]

Reax 907 [%] 15
Baykanol SL [%] 15 15 10
Geropon TA/72 [%] 5 5 5

Galoryl MT 804 [%] 1 1 1 1 1
Pergopak M[%] 5 3 3 2
Rhodorsil EP 6703 [%] 1 1 1 1
Mg0 [%] 1
Celite 209 S[%] 4 10.2

Kaolin W [%] 10.2 11.2 11.2 15.2 17.2
Talkum Luzenac 2 [%] 15.2
Total 100 100 100 100 100 100 100 100
Added water during the
30 25 25 20 20 15 12 25
preparation [%]


CA 02621631 2008-03-06
BCS OS 3078-Foreign Countries

-14-
Table 3:

Exa m ple No. 13 14 1 15 16 17 18 19 20
Preparation
Suspension stability
89 89 90 87 89 93 95 90
[%]
Wet-screening
0.020 0.010
150 pm
[%]
~ _- -_ -_ --- I
2W 15-1 C'
- -~_
I - - _ ,
Suspension stability
53 27 38 34 87 91 88 72
[%]
Wet-screening
0.030 21.5 0 0.13 0.12 0.005 0.005 0
150 [tm [%]
NV / 40 ('
4
Suspension stability
24.2 75 67 67 92 93 94 84
[%]
Wet-screening
0 0 0 0.016 0 0 0 0.023
150 m [%]

Table 2 compiles various formulations of trifloxystrobin in mixture with
tolylfluanid. The
preparation was accomplished as described further above, using a Fuji Paudal
laboratory extruder
type DG-1. Table 3 gives the test results of the exemplary formulations with
regard to suspension
stability and wet-screening residues. The tests were performed using the
methods described further
above. "Preparation" means that the test was performed shortly after the
preparation (as a rule after
not more than five days and storage at ambient temperature) of the sample,
while "2W/54 C" and
"4W/40 C" means that the samples were stored for 2 weeks at 54 C or for 4
weeks at 40 C and
then tested. The test results after storage over a relatively short period at
higher temperatures
permit an estimate of the stability of the formulation after storage at
conventional ambient
temperature over a prolonged period.

In compositions containing a combination of trifloxystrobin and tolylfluanid,
not only the screen
residues after wet screening, but also the suspension stability present a
problem. The results show
that only those samples which have been prepared using the dispersants
Baykanol SL and Reax
907 (Examples 17 - 20) exhibit satisfactory suspension stability and wet-
screening residues,
especially after storage at elevated temperatures. Baykanol SL is
particularly preferable.


CA 02621631 2008-03-06
BCS 05-3078-Foreign Countries

-15-
Kraftsperse EDF-350 is a lignosulphonate from Westvaco Corp., Charleston
Heights, SC, USA.
Geropon TA 72 is a sodium polycarbonate from Rhodia, Boulogne, France.

Galoryl MT 804 is a sodium di-butylnaphthalenesulphonate from Nufarm,
Melbourne,
Australia.

Pergopak M is a polymethylurea resin from Albemarle Corporation, Baton
Rouge, LA, USA.
Rhodorsil EP 6703 is a polydimethylsiloxane on starch from Rhodia, Boulogne,
France.
Celite 209 S is a diatomaceous earth from Lehmann & Voss, Hamburg, Germany.

Talkum Luzenac 2 is a magnesium hydrosilicate from Luzenac Europe, Paris,
France.

Kaolin W is an aluminohydrosilicate from Erbsloh Lohrheim GmbH & Co. KG,
Lohrheim,
Germany.

Kraftsperse DD-5, Kraftsperse DD-8, Kraftsperse DW-8, Kraftsperse EDF-
450, Reax
88B and Reax 907 are lignosulphonates from Westvaco Corp., Charleston
Heights, SC, USA.
Borresperse Na and Ufoxane 3 A are lignosulphonates from Borregaard,
Sarpsborg, Norway.
Morwet D 425 is a naphthalenesulphonic acid/formaldehyde condensate, sodium
salt, from
Akzo Nobel, Stenungsund, Sweden.

Galoryl DT 530 is a naphthalenesulphonic acid/formaldehyde condensate,
sodium salt, from
Nufarm, Melbourne, Australia.

Tersperse is a naphthalenesulphonic acid/formaldehyde condensate, sodium
salt, from
Huntsman, The Woodlands, Texas, USA.

Baykanol 9 SL is an alkylarylsulphonate from Lanxess, Leverkusen, Germany.

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 2006-08-31
(87) PCT Publication Date 2007-03-15
(85) National Entry 2008-03-06
Examination Requested 2011-08-29
Dead Application 2013-09-03

Abandonment History

Abandonment Date Reason Reinstatement Date
2008-09-02 FAILURE TO PAY APPLICATION MAINTENANCE FEE 2008-10-08
2012-08-31 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $400.00 2008-03-06
Reinstatement: Failure to Pay Application Maintenance Fees $200.00 2008-10-08
Maintenance Fee - Application - New Act 2 2008-09-02 $100.00 2008-10-08
Maintenance Fee - Application - New Act 3 2009-08-31 $100.00 2009-08-07
Maintenance Fee - Application - New Act 4 2010-08-31 $100.00 2010-08-09
Maintenance Fee - Application - New Act 5 2011-08-31 $200.00 2011-08-04
Request for Examination $800.00 2011-08-29
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Past Owners on Record
WOLF, HILMAR
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Cover Page 2008-06-04 1 29
Abstract 2008-03-06 1 9
Claims 2008-03-06 1 31
Description 2008-03-06 15 698
PCT 2008-03-06 4 194
Assignment 2008-03-06 4 115
Prosecution-Amendment 2011-08-29 2 73